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Mild and Diazo-Free Synthesis of Trifluoromethyl-Cyclopropanes Using Sulfonium Ylides.

Cyr P, Flynn-Robitaille J, Boissarie P, Marinier A

Medicinal Chemistry, Institute of Research in Immunology and Cancer , Université de Montréal , Montreal , QC H3C 3J7 , Canada.

The synthesis of several 1,1-disubstituted trifluoromethyl-cyclopropanes (TFCPs), known as tert-butyl bioisosteres, has been achieved from the reaction between trifluoromethylalkenes and unstabilized sulfonium ylides in yields of ≤97%. This method offers practical access to this cyclopropyl moiety of pharmacological interest, employing a commercially available reagent at low temperatures. The synthesis of cyclopropanes bearing other electron-withdrawing groups as well as trisubstituted TFCPs was also accomplished.

Org. Lett. 2019;21(7):2265-2268.

Pubmed ID: 30883143

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